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Infinite Jest by David Foster Wallace is a vast and sprawling novel that delves into themes of addiction, recovery, popular entertainment, and tennis. The book's 981 pages, along with extensive endnotes, present a labyrinthine mass of plot lines that intersect in intricate ways, revealing linguistic complexities and stylistic experimentation for which Wallace is renowned. The narrative threads, though disjointed at times, come together towards the end, offering a fictional DSM IV of American malaise and serving as a deep reflection on communication and human nature.

If you liked Infinite Jest, here are the top 100 books to read next:

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Showing 1 - 10 of 100 
  1. #1

    Gravity's Rainbow by Thomas Pynchon
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    "Gravity's Rainbow" by Thomas Pynchon is a complex and dense novel set in Europe at the end of World War II, focusing on the design, production, and dispatch of V 2 rockets by the German military. The story revolves around the quest of various characters to uncover the secret of a mysterious device named the Schwarzgerät, which is to be installed in a rocket with the serial number 00000. Pynchon's writing style is frequently digressive, subverting traditional elements of plot and character development, and incorporating detailed knowledge from various disciplines.

    The novel is known for its innovation and complexity, often praised for pushing the boundaries of postmodern writing. However, some readers find the book challenging due to the multitude of characters, intricate plotlines, and the author's tendency to jump about seemingly at random. Despite its challenging nature, "Gravity's Rainbow" is recognized for its poetic and beautiful moments, as well as its exploration of themes related to the quest for being and the breaking down of social constructions.

    It is too late. The Evacuation still proceeds, but it's all theatre. There are no lights inside the cars. No light anywhere. Above him lift girders old as an iron queen, and glass somewhere far above ...

  2. #2

    House of Leaves by Mark Z. Danielewski
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    House of Leaves by Mark Z. Danielewski is a complex and ambitious novel that delves into the mysterious record of a house that defies physics, expanding and lacking spatial boundaries. The story is told unconventionally through different perspectives, utilizing unique page layouts, sentences, paragraphs, and words to create imagery that parallels the narrative. The book also incorporates numerous footnotes that reference various elements, both real and imaginary, adding layers of depth to the storytelling.

    The narrative structure of the book weaves together multiple stories within stories, creating a layered and enthralling journey into the unknown. Readers are drawn into the tale of The Navidson Record, told through the lenses of Zampano and Johnny Truant, each contributing to the unfolding mystery of the house that challenges reality. The book's presentation and narrative style offer a blend of horror, academic critique, and metafictional elements, making it a compelling and thought-provoking read.

    §Provide examples of hand shadows ranging from crabs, snails, rabbits,and turtles to dragons, panthers, tigers, and kangaroos. Also includehippos, frogs, elephants, birds of paradise, dogs, cockatoos,...

  3. #3

    War and Peace by Leo Tolstoy
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    'War and Peace' by Leo Tolstoy is a sprawling epic chronicling the lives of multiple characters during the Napoleonic and French Wars. The novel delves into the struggles and heroism of the Russian people, set against the backdrop of war. Tolstoy weaves philosophical dialogues throughout the narrative, offering deep insights into human existence and the impact of historical events. The book is known for its intricate character development and detailed accounts of Russian history, making it a captivating read despite its length.

    Well, Prince, Genoa and Lucca are now no more than private estates of the Bonaparte family. No, I warn you, that if you do not tell me we are at war, if you again allow yourself to palliate all the in...

  4. #4

    Moby Dick by Herman Melville
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    Moby Dick by Herman Melville is a classic novel that delves into the world of whaling in the 19th century, focusing on the vengeful hunt of a white sperm whale named Moby Dick by Captain Ahab. The story is narrated through the eyes of Ishmael, a young man who joins the crew of the ship Pequod along with his friend Queequeg, a former cannibal. The novel offers detailed insights into the whaling industry, life in Nantucket, and the psychological complexities of the characters, particularly Captain Ahab.

    The writing style of Moby Dick is described as epic, humorous, sarcastic, and rich in variety. Herman Melville's prose is praised for its depth and complexity, transporting readers to the world of whaling with vivid descriptions of the sea, ships, whales, and the characters' inner turmoil. The novel weaves together elements of history, mythology, poetry, and humor, creating a literary masterpiece that explores themes of revenge, obsession, and the human condition.

    Call me Ishmael. Some years ago—never mind how long precisely—having little or no money in my purse, and nothing particular to interest me on shore, I thought I would sail about a little and see the w...

  5. #5

    Finnegans Wake by James Joyce
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    Finnegans Wake is a challenging and unconventional piece of literature, often described as a dreamlike stream of consciousness journey through the minds of various characters. The book is filled with complex wordplay, multi-layered meanings, and references to a wide range of cultural, historical, and mythological sources. It defies traditional narrative structures and presents a unique reading experience that requires careful attention and multiple readings to fully grasp its depth and richness.

    Every evening at lighting up o’clock sharp and until further notice in Feenichts Playhouse. (Bar and conveniences always open, Diddlem Club douncestears.) Entrancings: gads, a scrab; the quality, one ...

  6. Blood Meridian: Or the Evening Redness in the West by Cormac McCarthy is a brutal and violent tale set in the American Southwest and Mexico during the 19th century. The story follows a young man known as The Kid who joins a group of scalp hunters led by the enigmatic and ruthless Judge Holden. The book delves into themes of violence, survival, and the darkness of human nature, all portrayed through McCarthy's haunting and vivid prose. The narrative is bleak and unrelenting, showcasing the harsh realities of life on the border between Mexico and America, where evil takes on human form in the physical world.

    The book is described as a western where the Wild West is stripped of any heroic illusions, focusing instead on a group of merciless scalp hunters collecting bounties along the US-Mexico borderlands. McCarthy's writing style is elegant, detached, and breath-catching, rendering the beauty of the desert landscapes, the brutality of survival, and the emotional bankruptcy of the characters with exquisite detail. The characters, especially the enigmatic Judge Holden, provide a glimpse into mankind's addiction to violence, making the novel a gripping and thought-provoking exploration of morality and human nature.

    See the child. He is pale and thin, he wears a thin and ragged linen shirt. He stokes the scullery fire. Outside lie dark turned fields with rags of snow and darker woods beyond that harbor yet a few ...

  7. #7

    Pale Fire by Vladimir Nabokov
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    Pale Fire is a complex and unique novel that revolves around a 999-line poem written by John Shade, with added commentary and index by Charles Kinbote. The poem delves into Shade's personal life, particularly focusing on the death of his daughter, while Kinbote interprets it as a political commentary on the coup in his home country of Zenobia. The narrative unfolds through the interplay between Shade's poem and Kinbote's commentary, creating a multi-layered and intricate story that blurs the lines between reality and fiction.

    Nabokov's writing style in Pale Fire is characterized by its lush, pulpy prose that beautifully describes intricate details and creates vivid imagery. The novel's format challenges traditional storytelling by using the form of literary criticism to weave together the lives of three men: Shade, Kinbote, and Gradus. Through the use of unreliable narrators and metafictional elements, Nabokov crafts a narrative that is both humorous and thought-provoking, inviting readers to delve into the complexities of the text and uncover hidden meanings.

    Pale Fire, a poem in heroic couplets, of nine hundred ninety-nine lines, divided into four cantos, was composed by John Francis Shade (born July 5, 1898, died July 21, 1959) during the last twenty day...

  8. #8

    The Brothers Karamazov by Fyodor Dostoyevsky
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    'The Brothers Karamazov' by Fyodor Dostoyevsky is a classic Russian tale that delves into the lives of Fyodor Pavlovich Karamazov and his sons Ivan, Dmitri, and Alexei. The novel is known for its acute examination of the psychology of its main characters, as well as its exploration of Russian identity, family dynamics, and ethical debates. The book weaves together a murder mystery, a psychological thriller, a religious treatise, and a social commentary, all while portraying a dysfunctional family and the struggles of humanity.

    The writing style of 'The Brothers Karamazov' is described as deep, complex, philosophical, humane, and powerful. The book is praised for its sprawling narrative, great characters, and thought-provoking themes that encompass religion, morality, good vs. evil, and the essence of human nature. Despite its length and occasional tangents, readers appreciate the brilliance and relevance of the novel, which continues to challenge and inspire readers with its depth and complexity.

    Alexey Fyodorovitch Karamazov was the third son of Fyodor PavlovitchKaramazov, a land owner well known in our district in his own day, andstill remembered among us owing to his gloomy and tragic death...

  9. #9

    Ulysses by James Joyce
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    'Ulysses' by James Joyce is described as an experimental novel that follows the events of a single day, June 16th, 1904, in Dublin. The book delves into the lives of various characters, with a focus on Dublin school teacher Stephen Daedalus, his wife Molly Bloom, and her husband Leopold. The narrative is known for its intricate language play, stream of consciousness technique, and lack of traditional punctuation, which adds to the complexity and challenge of deciphering the plot. Readers mention that the book covers universal themes such as love, history, parenthood, friendship, and society, albeit in an obscure and oblique manner that requires deep reflection and integration to fully appreciate.

    STATELY, PLUMP BUCK MULLIGAN CAME FROM THE STAIRHEAD, bearing a bowl of lather on which a mirror and a razor lay crossed. A yellow dressinggown, ungirdled, was sustained gently behind him by the mild ...

  10. #10
    Catch-22
    Book 1 in the series:Catch-22

    Catch-22 - Catch-22 by Joseph Heller
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    'Catch-22' by Joseph Heller is a satirical novel set during World War II, focusing on the experiences of a bombardier named Yossarian. The story delves into the absurdity and insanity of military life, highlighting the struggles of individuals trying to navigate through a world where life is cheap and the rules seem designed to ensure no escape from the horrors of war. Through a fragmented narrative style, the author weaves a darkly humorous tale that provides insights into the futility of war and the importance of self-preservation amidst chaos.

    The writing style of 'Catch-22' is characterized by its witty banter, dark humor, and satirical take on the bureaucracy and illogical reasoning prevalent in wartime. The narrative jumps between characters, time periods, and locations, creating a chaotic yet engaging reading experience. Heller's exploration of the themes of insanity, morality, and the absurdity of life is delivered through a mix of laugh-out-loud moments and poignant reflections on the human condition.

    Yossarian was in the hospital with a pain in his liver that fell just short of being jaundice. The doctors were puzzled by the fact that it wasn’t quite jaundice. If it became jaundice they could trea...

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